#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:21:59 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284256 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/65/7246544.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7246544
loop_
_publ_author_name
'Barton, Benita'
'Trollip, Danica B.'
'Hosten, Eric C.'
_publ_section_title
;
 Host behaviour of two tricyclic fused systems in mixed anisole guest
 solvents
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              3013
_journal_page_last               3024
_journal_paper_doi               10.1039/D3CE00174A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         '2(C44 H40 N2), 3(C7 H8 O)'
_chemical_formula_sum            'C109 H104 N4 O3'
_chemical_formula_weight         1517.96
_chemical_name_systematic
;
N,N'-Bis(5-phenyl-10,11-dihydro-5-dibenzo[a,d]cycloheptenyl)ethylenediamine
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-02-13 deposited with the CCDC.	2023-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                107.750(2)
_cell_angle_beta                 93.267(2)
_cell_angle_gamma                102.939(2)
_cell_formula_units_Z            1
_cell_length_a                   12.3235(7)
_cell_length_b                   13.4341(8)
_cell_length_c                   13.8154(8)
_cell_measurement_reflns_used    9216
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.66
_cell_volume                     2103.6(2)
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'
_computing_structure_refinement
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            73977
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_min         1.645
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9578
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             810
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: anisole'
_exptl_crystal_size_max          0.770
_exptl_crystal_size_mid          0.646
_exptl_crystal_size_min          0.575
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0051(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     558
_refine_ls_number_reflns         10394
_refine_ls_number_restraints     68
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0487P)²+0.5683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1208
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8283
_reflns_number_total             10394
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00174a1.cif
_cod_data_source_block           ma169
_cod_depositor_comments
'Adding full bibliography for 7246542--7246544.cif.'
_cod_database_code               7246544
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.960
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.81021(8) 0.65233(9) 0.50430(7) 0.0359(2) Uani 1 1 d . . . . .
N2 N 0.83729(8) 0.59288(8) 0.28934(7) 0.0336(2) Uani 1 1 d . . . . .
C1 C 0.80434(9) 0.63292(9) 0.60439(8) 0.0328(2) Uani 1 1 d . . . . .
C2 C 0.92115(9) 0.67469(11) 0.46971(8) 0.0386(3) Uani 1 1 d . . . . .
H2A H 0.954497 0.614456 0.463326 0.046 Uiso 1 1 calc R U . . .
H2B H 0.970722 0.738883 0.519153 0.046 Uiso 1 1 calc R U . . .
C3 C 0.90560(9) 0.69153(9) 0.36656(8) 0.0362(2) Uani 1 1 d . . . . .
H3A H 0.869292 0.749837 0.372992 0.043 Uiso 1 1 calc R U . . .
H3B H 0.978464 0.711930 0.344934 0.043 Uiso 1 1 calc R U . . .
C4 C 0.78276(9) 0.60933(8) 0.19887(8) 0.0307(2) Uani 1 1 d . . . . .
C5 C 0.74892(12) 0.64267(12) 0.81545(9) 0.0490(3) Uani 1 1 d . . . . .
H5A H 0.713933 0.645564 0.877053 0.059 Uiso 1 1 calc R U . . .
H5B H 0.810447 0.707045 0.832070 0.059 Uiso 1 1 calc R U . . .
C6 C 0.79859(13) 0.54409(12) 0.78810(10) 0.0520(3) Uani 1 1 d . . . . .
H6A H 0.876344 0.569116 0.819771 0.062 Uiso 1 1 calc R U . . .
H6B H 0.759953 0.495333 0.821638 0.062 Uiso 1 1 calc R U . . .
C7 C 0.77397(12) 0.84984(10) 0.21139(11) 0.0490(3) Uani 1 1 d . . . . .
H7A H 0.844288 0.869296 0.256168 0.059 Uiso 1 1 calc R U . . .
H7B H 0.750505 0.915487 0.217323 0.059 Uiso 1 1 calc R U . . .
C8 C 0.79219(12) 0.79831(11) 0.10107(10) 0.0484(3) Uani 1 1 d . . . . .
H8A H 0.721399 0.751722 0.061889 0.058 Uiso 1 1 calc R U . . .
H8B H 0.816905 0.854554 0.070900 0.058 Uiso 1 1 calc R U . . .
C11 C 0.68781(9) 0.64230(9) 0.63565(8) 0.0344(2) Uani 1 1 d . . . . .
C12 C 0.66383(10) 0.64743(10) 0.73526(9) 0.0406(3) Uani 1 1 d . . . . .
C13 C 0.55747(12) 0.65654(11) 0.75958(11) 0.0514(3) Uani 1 1 d . . . . .
H13 H 0.541820 0.662857 0.825937 0.062 Uiso 1 1 calc R U . . .
C14 C 0.47462(12) 0.65644(12) 0.68774(13) 0.0547(3) Uani 1 1 d . . . . .
H14 H 0.404795 0.664138 0.706205 0.066 Uiso 1 1 calc R U . . .
C15 C 0.49592(11) 0.64494(11) 0.58913(12) 0.0490(3) Uani 1 1 d . . . . .
H15 H 0.439557 0.641600 0.539654 0.059 Uiso 1 1 calc R U . . .
C16 C 0.60191(10) 0.63829(10) 0.56339(10) 0.0400(3) Uani 1 1 d . . . . .
H16 H 0.615897 0.631005 0.496458 0.048 Uiso 1 1 calc R U . . .
C21 C 0.80535(9) 0.51537(9) 0.59293(8) 0.0347(2) Uani 1 1 d . . . . .
C22 C 0.79751(10) 0.47698(10) 0.67727(9) 0.0398(3) Uani 1 1 d . . . . .
C23 C 0.78910(11) 0.36715(11) 0.65939(11) 0.0486(3) Uani 1 1 d . . . . .
H23 H 0.784177 0.341214 0.714608 0.058 Uiso 1 1 calc R U . . .
C24 C 0.78781(11) 0.29588(11) 0.56328(12) 0.0526(3) Uani 1 1 d . . . . .
H24 H 0.782267 0.223304 0.554037 0.063 Uiso 1 1 calc R U . . .
C25 C 0.79484(11) 0.33346(11) 0.48117(11) 0.0492(3) Uani 1 1 d . . . . .
H25 H 0.794037 0.286286 0.415781 0.059 Uiso 1 1 calc R U . . .
C26 C 0.80311(9) 0.44185(10) 0.49611(9) 0.0402(3) Uani 1 1 d . . . . .
H26 H 0.807296 0.466242 0.439917 0.048 Uiso 1 1 calc R U . . .
C31 C 0.90093(10) 0.71793(10) 0.68217(8) 0.0367(2) Uani 1 1 d . . . . .
C32 C 0.89426(12) 0.82447(11) 0.71795(11) 0.0499(3) Uani 1 1 d . . . . .
H32 H 0.830008 0.842425 0.697703 0.060 Uiso 1 1 calc R U . . .
C33 C 0.98233(15) 0.90466(12) 0.78364(13) 0.0649(4) Uani 1 1 d . . . . .
H33 H 0.976516 0.975646 0.807575 0.078 Uiso 1 1 calc R U . . .
C34 C 1.07822(14) 0.87903(13) 0.81329(13) 0.0659(4) Uani 1 1 d . . . . .
H34 H 1.136829 0.932363 0.858081 0.079 Uiso 1 1 calc R U . . .
C35 C 1.08690(12) 0.77461(13) 0.77652(12) 0.0578(4) Uani 1 1 d . . . . .
H35 H 1.152112 0.757515 0.795774 0.069 Uiso 1 1 calc R U . . .
C36 C 0.99914(10) 0.69389(11) 0.71066(10) 0.0446(3) Uani 1 1 d . . . . .
H36 H 1.006371 0.623450 0.685603 0.054 Uiso 1 1 calc R U . . .
C41 C 0.68938(9) 0.66850(9) 0.23531(8) 0.0332(2) Uani 1 1 d . . . . .
C42 C 0.68646(10) 0.77448(10) 0.24510(9) 0.0388(2) Uani 1 1 d . . . . .
C43 C 0.59434(12) 0.81147(11) 0.28264(10) 0.0501(3) Uani 1 1 d . . . . .
H43 H 0.591532 0.881311 0.287071 0.060 Uiso 1 1 calc R U . . .
C44 C 0.50806(11) 0.74854(13) 0.31314(10) 0.0534(3) Uani 1 1 d . . . . .
H44 H 0.447977 0.775308 0.337535 0.064 Uiso 1 1 calc R U . . .
C45 C 0.51202(10) 0.64525(12) 0.30700(10) 0.0482(3) Uani 1 1 d . . . . .
H45 H 0.455421 0.601908 0.328780 0.058 Uiso 1 1 calc R U . . .
C46 C 0.60083(10) 0.60656(10) 0.26817(9) 0.0404(3) Uani 1 1 d . . . . .
H46 H 0.602003 0.536308 0.263604 0.048 Uiso 1 1 calc R U . . .
C51 C 0.87792(9) 0.65612(9) 0.14340(8) 0.0329(2) Uani 1 1 d . . . . .
C52 C 0.87801(10) 0.73311(10) 0.09395(8) 0.0386(2) Uani 1 1 d . . . . .
C53 C 0.96665(12) 0.75652(12) 0.03863(10) 0.0499(3) Uani 1 1 d . . . . .
H53 H 0.966862 0.807635 0.005890 0.060 Uiso 1 1 calc R U . . .
C54 C 1.05331(12) 0.70665(13) 0.03100(11) 0.0550(3) Uani 1 1 d . . . . .
H54 H 1.110488 0.723171 -0.007015 0.066 Uiso 1 1 calc R U . . .
C55 C 1.05430(11) 0.63201(12) 0.08034(10) 0.0496(3) Uani 1 1 d . . . . .
H55 H 1.113008 0.598507 0.076898 0.060 Uiso 1 1 calc R U . . .
C56 C 0.96745(10) 0.60695(10) 0.13521(9) 0.0407(3) Uani 1 1 d . . . . .
H56 H 0.968645 0.555795 0.167650 0.049 Uiso 1 1 calc R U . . .
C61 C 0.72251(9) 0.49747(9) 0.12099(8) 0.0343(2) Uani 1 1 d . . . . .
C62 C 0.73240(11) 0.40147(10) 0.13379(10) 0.0428(3) Uani 1 1 d . . . . .
H62 H 0.778388 0.403080 0.190288 0.051 Uiso 1 1 calc R U . . .
C63 C 0.67420(12) 0.30252(11) 0.06294(12) 0.0540(3) Uani 1 1 d . . . . .
H63 H 0.680650 0.238744 0.073298 0.065 Uiso 1 1 calc R U . . .
C64 C 0.60753(13) 0.29811(12) -0.02187(12) 0.0591(4) Uani 1 1 d . . . . .
H64 H 0.569094 0.231806 -0.069092 0.071 Uiso 1 1 calc R U . . .
C65 C 0.59802(14) 0.39312(13) -0.03648(11) 0.0611(4) Uani 1 1 d . . . . .
H65 H 0.553492 0.390939 -0.094124 0.073 Uiso 1 1 calc R U . . .
C66 C 0.65459(12) 0.49164(11) 0.03445(10) 0.0492(3) Uani 1 1 d . . . . .
H66 H 0.647049 0.555115 0.024066 0.059 Uiso 1 1 calc R U . . .
H1 H 0.7823(12) 0.7097(12) 0.5075(11) 0.044(4) Uiso 1 1 d . . . . .
H2 H 0.7850(12) 0.5643(11) 0.3201(11) 0.042(4) Uiso 1 1 d . . . . .
O7 O 0.44732(12) 1.00400(11) 0.33262(11) 0.0882(4) Uani 1 1 d D . . . .
C71 C 0.34036(15) 0.99300(12) 0.35756(12) 0.0611(4) Uani 1 1 d D . . . .
C72 C 0.31154(17) 1.05424(14) 0.44719(13) 0.0724(5) Uani 1 1 d D . . . .
H72 H 0.366222 1.108816 0.495391 0.087 Uiso 1 1 calc R U . . .
C73 C 0.20150(19) 1.03417(16) 0.46492(15) 0.0832(6) Uani 1 1 d D . . . .
H73 H 0.182478 1.075024 0.525942 0.100 Uiso 1 1 calc R U . . .
C74 C 0.11925(18) 0.95526(15) 0.39461(16) 0.0783(5) Uani 1 1 d D . . . .
H74 H 0.045025 0.942614 0.407510 0.094 Uiso 1 1 calc R U . . .
C75 C 0.14770(17) 0.89538(14) 0.30527(14) 0.0709(5) Uani 1 1 d D . . . .
H75 H 0.092242 0.842135 0.256731 0.085 Uiso 1 1 calc R U . . .
C76 C 0.25701(17) 0.91290(13) 0.28641(12) 0.0673(4) Uani 1 1 d D . . . .
H76 H 0.275474 0.870934 0.225654 0.081 Uiso 1 1 calc R U . . .
C77 C 0.53467(19) 1.08837(16) 0.4002(2) 0.0987(7) Uani 1 1 d D . . . .
H77A H 0.603126 1.091243 0.370075 0.148 Uiso 1 1 calc R U . . .
H77B H 0.544951 1.075020 0.464099 0.148 Uiso 1 1 calc R U . . .
H77C H 0.515091 1.155977 0.412178 0.148 Uiso 1 1 calc R U . . .
O8 O 0.3181(4) 0.0248(5) -0.0069(3) 0.1038(12) Uani 0.5 1 d D . P A -1
C81 C 0.4227(2) 0.0083(3) -0.0048(3) 0.0760(11) Uani 0.5 1 d DG . P A -1
C82 C 0.4893(4) 0.0179(3) 0.0839(3) 0.0950(19) Uani 0.5 1 d DG . P A -1
H82 H 0.463398 0.038233 0.147083 0.114 Uiso 0.5 1 calc R U P A -1
C83 C 0.5946(3) -0.0030(5) 0.0780(5) 0.141(3) Uani 0.5 1 d DG . P A -1
H83 H 0.639231 0.003371 0.137254 0.170 Uiso 0.5 1 calc R U P A -1
C84 C 0.6333(3) -0.0335(5) -0.0165(6) 0.142(3) Uani 0.5 1 d DG . P A -1
H84 H 0.703834 -0.047433 -0.020475 0.170 Uiso 0.5 1 calc R U P A -1
C85 C 0.5667(4) -0.0430(4) -0.1051(4) 0.111(2) Uani 0.5 1 d DG . P A -1
H85 H 0.592605 -0.063376 -0.168377 0.134 Uiso 0.5 1 calc R U P A -1
C86 C 0.4614(3) -0.0221(3) -0.0993(3) 0.0913(17) Uani 0.5 1 d DG . P A -1
H86 H 0.416771 -0.028515 -0.158550 0.110 Uiso 0.5 1 calc R U P A -1
C87 C 0.2697(5) 0.0483(5) 0.0844(4) 0.1123(16) Uani 0.5 1 d D . P A -1
H87A H 0.195687 0.056689 0.070337 0.168 Uiso 0.5 1 calc R U P A -1
H87B H 0.315303 0.113980 0.133173 0.168 Uiso 0.5 1 calc R U P A -1
H87C H 0.264977 -0.009845 0.111943 0.168 Uiso 0.5 1 calc R U P A -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 118.03(8) . . ?
C2 N1 H1 106.5(9) . . ?
C1 N1 H1 108.1(9) . . ?
C3 N2 C4 114.93(9) . . ?
C3 N2 H2 106.5(9) . . ?
C4 N2 H2 108.6(9) . . ?
N1 C1 C31 107.93(8) . . ?
N1 C1 C21 110.94(9) . . ?
C31 C1 C21 113.81(9) . . ?
N1 C1 C11 107.31(8) . . ?
C31 C1 C11 112.26(9) . . ?
C21 C1 C11 104.42(8) . . ?
N1 C2 C3 108.26(9) . . ?
N1 C2 H2A 110.0 . . ?
C3 C2 H2A 110.0 . . ?
N1 C2 H2B 110.0 . . ?
C3 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
N2 C3 C2 110.72(9) . . ?
N2 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N2 C4 C61 108.50(8) . . ?
N2 C4 C51 107.40(8) . . ?
C61 C4 C51 104.36(8) . . ?
N2 C4 C41 107.64(8) . . ?
C61 C4 C41 106.71(8) . . ?
C51 C4 C41 121.66(9) . . ?
C12 C5 C6 117.04(11) . . ?
C12 C5 H5A 108.0 . . ?
C6 C5 H5A 108.0 . . ?
C12 C5 H5B 108.0 . . ?
C6 C5 H5B 108.0 . . ?
H5A C5 H5B 107.3 . . ?
C22 C6 C5 121.41(11) . . ?
C22 C6 H6A 107.0 . . ?
C5 C6 H6A 107.0 . . ?
C22 C6 H6B 107.0 . . ?
C5 C6 H6B 107.0 . . ?
H6A C6 H6B 106.7 . . ?
C42 C7 C8 111.51(11) . . ?
C42 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C42 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C52 C8 C7 112.22(11) . . ?
C52 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C52 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C16 C11 C12 118.69(11) . . ?
C16 C11 C1 120.28(10) . . ?
C12 C11 C1 120.88(10) . . ?
C13 C12 C11 118.49(12) . . ?
C13 C12 C5 119.35(11) . . ?
C11 C12 C5 122.15(11) . . ?
C14 C13 C12 121.79(12) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C15 C14 C13 119.65(12) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 119.76(13) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 121.44(12) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C26 C21 C22 118.42(11) . . ?
C26 C21 C1 119.96(10) . . ?
C22 C21 C1 121.33(10) . . ?
C23 C22 C21 118.14(12) . . ?
C23 C22 C6 115.62(11) . . ?
C21 C22 C6 126.24(11) . . ?
C24 C23 C22 122.61(13) . . ?
C24 C23 H23 118.7 . . ?
C22 C23 H23 118.7 . . ?
C25 C24 C23 119.10(13) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 119.81(13) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C21 121.92(12) . . ?
C25 C26 H26 119.0 . . ?
C21 C26 H26 119.0 . . ?
C36 C31 C32 118.43(11) . . ?
C36 C31 C1 122.24(11) . . ?
C32 C31 C1 119.05(11) . . ?
C31 C32 C33 120.86(13) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C34 C33 C32 119.99(15) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C35 C34 C33 119.69(13) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 C36 120.65(14) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C31 C36 C35 120.33(13) . . ?
C31 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C42 C41 C46 117.19(10) . . ?
C42 C41 C4 128.97(10) . . ?
C46 C41 C4 113.71(10) . . ?
C41 C42 C43 118.95(12) . . ?
C41 C42 C7 123.35(10) . . ?
C43 C42 C7 117.60(11) . . ?
C44 C43 C42 122.56(13) . . ?
C44 C43 H43 118.7 . . ?
C42 C43 H43 118.7 . . ?
C43 C44 C45 118.92(12) . . ?
C43 C44 H44 120.5 . . ?
C45 C44 H44 120.5 . . ?
C44 C45 C46 119.37(12) . . ?
C44 C45 H45 120.3 . . ?
C46 C45 H45 120.3 . . ?
C45 C46 C41 122.96(12) . . ?
C45 C46 H46 118.5 . . ?
C41 C46 H46 118.5 . . ?
C56 C51 C52 117.89(10) . . ?
C56 C51 C4 114.57(10) . . ?
C52 C51 C4 127.25(10) . . ?
C53 C52 C51 118.73(12) . . ?
C53 C52 C8 116.81(11) . . ?
C51 C52 C8 124.36(10) . . ?
C54 C53 C52 122.39(13) . . ?
C54 C53 H53 118.8 . . ?
C52 C53 H53 118.8 . . ?
C53 C54 C55 119.12(12) . . ?
C53 C54 H54 120.4 . . ?
C55 C54 H54 120.4 . . ?
C54 C55 C56 119.71(13) . . ?
C54 C55 H55 120.1 . . ?
C56 C55 H55 120.1 . . ?
C55 C56 C51 122.16(12) . . ?
C55 C56 H56 118.9 . . ?
C51 C56 H56 118.9 . . ?
C62 C61 C66 117.89(11) . . ?
C62 C61 C4 122.72(10) . . ?
C66 C61 C4 119.39(10) . . ?
C61 C62 C63 120.69(12) . . ?
C61 C62 H62 119.7 . . ?
C63 C62 H62 119.7 . . ?
C64 C63 C62 120.71(13) . . ?
C64 C63 H63 119.6 . . ?
C62 C63 H63 119.6 . . ?
C63 C64 C65 119.30(13) . . ?
C63 C64 H64 120.4 . . ?
C65 C64 H64 120.4 . . ?
C64 C65 C66 120.16(13) . . ?
C64 C65 H65 119.9 . . ?
C66 C65 H65 119.9 . . ?
C65 C66 C61 121.23(13) . . ?
C65 C66 H66 119.4 . . ?
C61 C66 H66 119.4 . . ?
C71 O7 C77 118.40(16) . . ?
O7 C71 C72 124.72(16) . . ?
O7 C71 C76 116.19(15) . . ?
C72 C71 C76 119.09(18) . . ?
C73 C72 C71 119.54(17) . . ?
C73 C72 H72 120.2 . . ?
C71 C72 H72 120.2 . . ?
C74 C73 C72 121.34(18) . . ?
C74 C73 H73 119.3 . . ?
C72 C73 H73 119.3 . . ?
C75 C74 C73 119.1(2) . . ?
C75 C74 H74 120.5 . . ?
C73 C74 H74 120.5 . . ?
C74 C75 C76 120.68(17) . . ?
C74 C75 H75 119.7 . . ?
C76 C75 H75 119.7 . . ?
C75 C76 C71 120.27(16) . . ?
C75 C76 H76 119.9 . . ?
C71 C76 H76 119.9 . . ?
O7 C77 H77A 109.5 . . ?
O7 C77 H77B 109.5 . . ?
H77A C77 H77B 109.5 . . ?
O7 C77 H77C 109.5 . . ?
H77A C77 H77C 109.5 . . ?
H77B C77 H77C 109.5 . . ?
C81 O8 C87 119.3(4) . . ?
O8 C81 C82 124.2(3) . . ?
O8 C81 C86 115.8(3) . . ?
C82 C81 C86 120.0 . . ?
C81 C82 C83 120.0 . . ?
C81 C82 H82 120.0 . . ?
C83 C82 H82 120.0 . . ?
C84 C83 C82 120.0 . . ?
C84 C83 H83 120.0 . . ?
C82 C83 H83 120.0 . . ?
C83 C84 C85 120.0 . . ?
C83 C84 H84 120.0 . . ?
C85 C84 H84 120.0 . . ?
C86 C85 C84 120.0 . . ?
C86 C85 H85 120.0 . . ?
C84 C85 H85 120.0 . . ?
C85 C86 C81 120.0 . . ?
C85 C86 H86 120.0 . . ?
C81 C86 H86 120.0 . . ?
O8 C87 H87A 109.5 . . ?
O8 C87 H87B 109.5 . . ?
H87A C87 H87B 109.5 . . ?
O8 C87 H87C 109.5 . . ?
H87A C87 H87C 109.5 . . ?
H87B C87 H87C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.4717(14) . ?
N1 C1 1.4860(13) . ?
N1 H1 0.902(15) . ?
N2 C3 1.4626(14) . ?
N2 C4 1.4838(13) . ?
N2 H2 0.874(14) . ?
C1 C31 1.5404(15) . ?
C1 C21 1.5413(16) . ?
C1 C11 1.5437(15) . ?
C2 C3 1.5177(15) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C61 1.5461(15) . ?
C4 C51 1.5568(14) . ?
C4 C41 1.5625(15) . ?
C5 C12 1.5073(18) . ?
C5 C6 1.535(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C22 1.5192(18) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C42 1.5035(18) . ?
C7 C8 1.5224(19) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C52 1.5065(18) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C11 C16 1.3934(16) . ?
C11 C12 1.4084(16) . ?
C12 C13 1.3939(18) . ?
C13 C14 1.382(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.3878(17) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C26 1.3941(16) . ?
C21 C22 1.4106(16) . ?
C22 C23 1.3982(18) . ?
C23 C24 1.377(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.375(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.3861(18) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C31 C36 1.3864(17) . ?
C31 C32 1.3877(18) . ?
C32 C33 1.389(2) . ?
C32 H32 0.9300 . ?
C33 C34 1.377(2) . ?
C33 H33 0.9300 . ?
C34 C35 1.370(2) . ?
C34 H34 0.9300 . ?
C35 C36 1.3909(19) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C41 C42 1.3975(16) . ?
C41 C46 1.4034(16) . ?
C42 C43 1.4027(17) . ?
C43 C44 1.374(2) . ?
C43 H43 0.9300 . ?
C44 C45 1.376(2) . ?
C44 H44 0.9300 . ?
C45 C46 1.3810(17) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C51 C56 1.4006(16) . ?
C51 C52 1.4025(16) . ?
C52 C53 1.4014(17) . ?
C53 C54 1.375(2) . ?
C53 H53 0.9300 . ?
C54 C55 1.375(2) . ?
C54 H54 0.9300 . ?
C55 C56 1.3857(17) . ?
C55 H55 0.9300 . ?
C56 H56 0.9300 . ?
C61 C62 1.3842(16) . ?
C61 C66 1.3913(17) . ?
C62 C63 1.3925(18) . ?
C62 H62 0.9300 . ?
C63 C64 1.370(2) . ?
C63 H63 0.9300 . ?
C64 C65 1.380(2) . ?
C64 H64 0.9300 . ?
C65 C66 1.3843(19) . ?
C65 H65 0.9300 . ?
C66 H66 0.9300 . ?
O7 C71 1.369(2) . ?
O7 C77 1.417(2) . ?
C71 C72 1.377(2) . ?
C71 C76 1.387(2) . ?
C72 C73 1.373(3) . ?
C72 H72 0.9300 . ?
C73 C74 1.369(3) . ?
C73 H73 0.9300 . ?
C74 C75 1.365(3) . ?
C74 H74 0.9300 . ?
C75 C76 1.369(3) . ?
C75 H75 0.9300 . ?
C76 H76 0.9300 . ?
C77 H77A 0.9600 . ?
C77 H77B 0.9600 . ?
C77 H77C 0.9600 . ?
O8 C81 1.355(4) . ?
O8 C87 1.404(6) . ?
C81 C82 1.3900 . ?
C81 C86 1.3900 . ?
C82 C83 1.3900 . ?
C82 H82 0.9300 . ?
C83 C84 1.3900 . ?
C83 H83 0.9300 . ?
C84 C85 1.3900 . ?
C84 H84 0.9300 . ?
C85 C86 1.3900 . ?
C85 H85 0.9300 . ?
C86 H86 0.9300 . ?
C87 H87A 0.9600 . ?
C87 H87B 0.9600 . ?
C87 H87C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 N1 0.874(14) 2.425(14) 2.8904(13) 113.8(11) . yes
C16 H16 N1 0.93 2.34 2.7217(15) 104 . yes
C26 H26 N1 0.93 2.38 2.7764(17) 106 . yes
C56 H56 N2 0.93 2.42 2.7644(15) 101 . yes
C62 H62 N2 0.93 2.41 2.7797(16) 103 . yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 C31 43.90(13) . . . . ?
C2 N1 C1 C21 -81.42(12) . . . . ?
C2 N1 C1 C11 165.09(10) . . . . ?
C1 N1 C2 C3 179.98(10) . . . . ?
C4 N2 C3 C2 158.85(9) . . . . ?
N1 C2 C3 N2 -63.58(13) . . . . ?
C3 N2 C4 C61 175.30(9) . . . . ?
C3 N2 C4 C51 63.03(11) . . . . ?
C3 N2 C4 C41 -69.58(11) . . . . ?
C12 C5 C6 C22 21.78(19) . . . . ?
C42 C7 C8 C52 -86.99(14) . . . . ?
N1 C1 C11 C16 16.04(14) . . . . ?
C31 C1 C11 C16 134.47(11) . . . . ?
C21 C1 C11 C16 -101.78(12) . . . . ?
N1 C1 C11 C12 -168.42(10) . . . . ?
C31 C1 C11 C12 -50.00(14) . . . . ?
C21 C1 C11 C12 73.76(12) . . . . ?
C16 C11 C12 C13 -4.79(17) . . . . ?
C1 C11 C12 C13 179.60(11) . . . . ?
C16 C11 C12 C5 174.81(12) . . . . ?
C1 C11 C12 C5 -0.80(18) . . . . ?
C6 C5 C12 C13 123.24(14) . . . . ?
C6 C5 C12 C11 -56.36(17) . . . . ?
C11 C12 C13 C14 2.5(2) . . . . ?
C5 C12 C13 C14 -177.09(13) . . . . ?
C12 C13 C14 C15 1.3(2) . . . . ?
C13 C14 C15 C16 -2.8(2) . . . . ?
C14 C15 C16 C11 0.4(2) . . . . ?
C12 C11 C16 C15 3.41(18) . . . . ?
C1 C11 C16 C15 179.04(11) . . . . ?
N1 C1 C21 C26 -4.58(13) . . . . ?
C31 C1 C21 C26 -126.53(11) . . . . ?
C11 C1 C21 C26 110.72(11) . . . . ?
N1 C1 C21 C22 -178.34(9) . . . . ?
C31 C1 C21 C22 59.72(13) . . . . ?
C11 C1 C21 C22 -63.03(12) . . . . ?
C26 C21 C22 C23 0.68(16) . . . . ?
C1 C21 C22 C23 174.53(10) . . . . ?
C26 C21 C22 C6 179.92(12) . . . . ?
C1 C21 C22 C6 -6.23(18) . . . . ?
C5 C6 C22 C23 -148.53(13) . . . . ?
C5 C6 C22 C21 32.2(2) . . . . ?
C21 C22 C23 C24 -0.24(19) . . . . ?
C6 C22 C23 C24 -179.56(12) . . . . ?
C22 C23 C24 C25 -0.1(2) . . . . ?
C23 C24 C25 C26 0.03(19) . . . . ?
C24 C25 C26 C21 0.44(19) . . . . ?
C22 C21 C26 C25 -0.79(17) . . . . ?
C1 C21 C26 C25 -174.73(10) . . . . ?
N1 C1 C31 C36 -101.89(12) . . . . ?
C21 C1 C31 C36 21.71(15) . . . . ?
C11 C1 C31 C36 140.05(11) . . . . ?
N1 C1 C31 C32 72.04(13) . . . . ?
C21 C1 C31 C32 -164.37(11) . . . . ?
C11 C1 C31 C32 -46.02(14) . . . . ?
C36 C31 C32 C33 -2.2(2) . . . . ?
C1 C31 C32 C33 -176.35(13) . . . . ?
C31 C32 C33 C34 0.6(2) . . . . ?
C32 C33 C34 C35 1.0(3) . . . . ?
C33 C34 C35 C36 -0.9(2) . . . . ?
C32 C31 C36 C35 2.24(19) . . . . ?
C1 C31 C36 C35 176.20(11) . . . . ?
C34 C35 C36 C31 -0.7(2) . . . . ?
N2 C4 C41 C42 110.04(12) . . . . ?
C61 C4 C41 C42 -133.65(11) . . . . ?
C51 C4 C41 C42 -14.35(16) . . . . ?
N2 C4 C41 C46 -65.59(11) . . . . ?
C61 C4 C41 C46 50.72(12) . . . . ?
C51 C4 C41 C46 170.02(9) . . . . ?
C46 C41 C42 C43 -2.60(16) . . . . ?
C4 C41 C42 C43 -178.10(11) . . . . ?
C46 C41 C42 C7 -178.75(11) . . . . ?
C4 C41 C42 C7 5.75(19) . . . . ?
C8 C7 C42 C41 51.88(17) . . . . ?
C8 C7 C42 C43 -124.32(12) . . . . ?
C41 C42 C43 C44 1.96(19) . . . . ?
C7 C42 C43 C44 178.33(13) . . . . ?
C42 C43 C44 C45 0.2(2) . . . . ?
C43 C44 C45 C46 -1.6(2) . . . . ?
C44 C45 C46 C41 0.82(19) . . . . ?
C42 C41 C46 C45 1.29(17) . . . . ?
C4 C41 C46 C45 177.47(10) . . . . ?
N2 C4 C51 C56 42.58(12) . . . . ?
C61 C4 C51 C56 -72.48(11) . . . . ?
C41 C4 C51 C56 167.08(10) . . . . ?
N2 C4 C51 C52 -143.75(11) . . . . ?
C61 C4 C51 C52 101.19(12) . . . . ?
C41 C4 C51 C52 -19.25(16) . . . . ?
C56 C51 C52 C53 0.37(17) . . . . ?
C4 C51 C52 C53 -173.12(11) . . . . ?
C56 C51 C52 C8 -175.81(12) . . . . ?
C4 C51 C52 C8 10.70(18) . . . . ?
C7 C8 C52 C53 -127.43(12) . . . . ?
C7 C8 C52 C51 48.82(17) . . . . ?
C51 C52 C53 C54 0.1(2) . . . . ?
C8 C52 C53 C54 176.56(13) . . . . ?
C52 C53 C54 C55 -0.8(2) . . . . ?
C53 C54 C55 C56 1.1(2) . . . . ?
C54 C55 C56 C51 -0.7(2) . . . . ?
C52 C51 C56 C55 -0.09(18) . . . . ?
C4 C51 C56 C55 174.22(11) . . . . ?
N2 C4 C61 C62 -6.56(14) . . . . ?
C51 C4 C61 C62 107.72(12) . . . . ?
C41 C4 C61 C62 -122.29(11) . . . . ?
N2 C4 C61 C66 172.96(10) . . . . ?
C51 C4 C61 C66 -72.77(13) . . . . ?
C41 C4 C61 C66 57.22(13) . . . . ?
C66 C61 C62 C63 -1.21(18) . . . . ?
C4 C61 C62 C63 178.31(11) . . . . ?
C61 C62 C63 C64 1.2(2) . . . . ?
C62 C63 C64 C65 -0.3(2) . . . . ?
C63 C64 C65 C66 -0.6(2) . . . . ?
C64 C65 C66 C61 0.5(2) . . . . ?
C62 C61 C66 C65 0.4(2) . . . . ?
C4 C61 C66 C65 -179.16(13) . . . . ?
C77 O7 C71 C72 -4.0(3) . . . . ?
C77 O7 C71 C76 176.74(17) . . . . ?
O7 C71 C72 C73 -178.49(17) . . . . ?
C76 C71 C72 C73 0.7(3) . . . . ?
C71 C72 C73 C74 -0.9(3) . . . . ?
C72 C73 C74 C75 0.1(3) . . . . ?
C73 C74 C75 C76 0.7(3) . . . . ?
C74 C75 C76 C71 -0.8(3) . . . . ?
O7 C71 C76 C75 179.39(16) . . . . ?
C72 C71 C76 C75 0.1(2) . . . . ?
C87 O8 C81 C82 -3.1(8) . . . . ?
C87 O8 C81 C86 175.5(4) . . . . ?
O8 C81 C82 C83 178.6(6) . . . . ?
C86 C81 C82 C83 0.0 . . . . ?
C81 C82 C83 C84 0.0 . . . . ?
C82 C83 C84 C85 0.0 . . . . ?
C83 C84 C85 C86 0.0 . . . . ?
C84 C85 C86 C81 0.0 . . . . ?
O8 C81 C86 C85 -178.7(5) . . . . ?
C82 C81 C86 C85 0.0 . . . . ?
